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549-18-8

549-18-8 structure
549-18-8 structure
  • Name: Amitriptyline Hydrochloride
  • Chemical Name: Amitriptyline hydrochloride
  • CAS Number: 549-18-8
  • Molecular Formula: C20H24ClN
  • Molecular Weight: 313.864
  • Catalog: API Nervous system medication Antidepressant, manic
  • Create Date: 2018-05-23 08:00:00
  • Modify Date: 2024-01-02 21:13:23
  • Amitriptyline Hydrochloride is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA).Target: OthersAmitriptyline acts primarily as a serotonin-norepinephrine reuptake inhibitor, with strong actions on the serotonin transporter and moderate effects on the norepinephrine transporter. It has negligible influence on the dopamine transporter and therefore does not affect dopamine reuptake, being nearly 1,000 times weaker on it than on serotonin [1]. Amitriptyline additionally functions as a 5-HT2A, 5-HT2C, 5-HT3, 5-HT6, 5-HT7, α1-adrenergic, H1, H2, and mACh receptorantagonist, and σ1 receptor agonist. It has also been shown to be a relatively weak NMDA receptor negative allosteric modulator at the same binding site as phencyclidine. Amitriptyline inhibits sodium channels, L-type calcium channels, and Kv1.1, Kv7.2, and Kv7.3 voltage-gated potassium channels, and therefore acts as a sodium, calcium, and potassium channel blocker as well [2]. Recently, amitriptyline has been demonstrated to act as an agonist of the TrkA and TrkB receptors. It promotes the heterodimerization of these proteins in the absence of NGF and has potent neurotrophic activity both in-vivo and in-vitro in mouse models [3].
Name Amitriptyline hydrochloride
Synonyms Amitriptyline Hydrochloride
3-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylidene)-N,N-dimethylpropan-1-amine,hydrochloride
3-(10,11-Dihydro-5H-dibenzo[a,d][7]annulen-5-yliden)-N,N-dimethylpropan-1-aminhydrochlorid
3-(10,11-Dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine hydrochloride (1:1)
EINECS 208-964-6
1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride (1:1)
1-propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride
MFCD00012537
Amitriptyline HCl
3-(10,11-dihydro-5H-dibenzo[a,d][7]annulén-5-ylidène)-N,N-diméthylpropan-1-amine chlorhydrate
3-(10,11-Dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethyl-1-propanamine hydrochloride (1:1)
3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine hydrochloride
5-(3-Dimethylaminopropylidene)dibenzo[a,d][1,4]cycloheptadiene hydrochloride
10,11-Dihydro-N,N-dimethyl-5H-dibenzo[a,d]cycloheptene-δ5,γ-propylamine hydrochloride
Amitriptyline (hydrochloride)
Description Amitriptyline Hydrochloride is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA).Target: OthersAmitriptyline acts primarily as a serotonin-norepinephrine reuptake inhibitor, with strong actions on the serotonin transporter and moderate effects on the norepinephrine transporter. It has negligible influence on the dopamine transporter and therefore does not affect dopamine reuptake, being nearly 1,000 times weaker on it than on serotonin [1]. Amitriptyline additionally functions as a 5-HT2A, 5-HT2C, 5-HT3, 5-HT6, 5-HT7, α1-adrenergic, H1, H2, and mACh receptorantagonist, and σ1 receptor agonist. It has also been shown to be a relatively weak NMDA receptor negative allosteric modulator at the same binding site as phencyclidine. Amitriptyline inhibits sodium channels, L-type calcium channels, and Kv1.1, Kv7.2, and Kv7.3 voltage-gated potassium channels, and therefore acts as a sodium, calcium, and potassium channel blocker as well [2]. Recently, amitriptyline has been demonstrated to act as an agonist of the TrkA and TrkB receptors. It promotes the heterodimerization of these proteins in the absence of NGF and has potent neurotrophic activity both in-vivo and in-vitro in mouse models [3].
Related Catalog
References

[1]. Tatsumi, M., et al., Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol, 1997. 340(2-3): p. 249-58.

[2]. http://en.wikipedia.org/wiki/Amitriptyline

[3]. Jang, S.W., et al., Amitriptyline is a TrkA and TrkB receptor agonist that promotes TrkA/TrkB heterodimerization and has potent neurotrophic activity. Chem Biol, 2009. 16(6): p. 644-56.
Density 1.076g/cm3
Boiling Point 398.2ºC at 760 mmHg
Melting Point 196-197°C
Molecular Formula C20H24ClN
Molecular Weight 313.864
Flash Point 11 °C
Exact Mass 313.159729
PSA 3.24000
LogP 4.97060
Storage condition 2-8°C
Water Solubility H2O: soluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HO9450000
CHEMICAL NAME :
5H-Dibenzo(a,d)cycloheptene-delta(sup 5),gamma-propylamine, 10,11-dihydro-N,N-dimethyl-, hydrochloride
CAS REGISTRY NUMBER :
549-18-8
LAST UPDATED :
199707
DATA ITEMS CITED :
39
MOLECULAR FORMULA :
C20-H23-N.Cl-H
MOLECULAR WEIGHT :
313.90
WISWESSER LINE NOTATION :
L C676 BY&T&J BU3N1&1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
58 mg/kg
TOXIC EFFECTS :
Behavioral - coma Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
714 ug/kg/1D-I
TOXIC EFFECTS :
Behavioral - alteration of operant conditioning Behavioral - changes in psychophysiological tests
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
60 mg/kg/3W-I
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Behavioral - withdrawal
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
62500 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
4167 ug/kg
TOXIC EFFECTS :
Behavioral - sleep Behavioral - hallucinations, distorted perceptions Behavioral - muscle contraction or spasticity
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - muscle contraction or spasticity Behavioral - coma
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
62500 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
19 mg/kg
TOXIC EFFECTS :
Behavioral - coma Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
14286 ug/kg
TOXIC EFFECTS :
Behavioral - coma Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
240 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
67 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
385 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
14 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
140 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
65 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - cyanosis
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
21 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>27 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>23 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
20300 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
37 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
9900 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
52 mg/kg
TOXIC EFFECTS :
Cardiac - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3200 mg/kg/32D-C
TOXIC EFFECTS :
Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
24640 mg/kg/1Y-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
220 mg/kg
SEX/DURATION :
female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
70 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
60 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
60 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
60 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
70300 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
60 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - body wall
TYPE OF TEST :
Sex chromosome loss and nondisjunction

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
70 mg/kg/5D
REFERENCE :
IMSCE2 IRCS Medical Science. (Lancaster, UK) V.12-14, 1984-86. For publisher information, see MSCREJ. Volume(issue)/page/year: 14,579,1986 *** REVIEWS *** TOXICOLOGY REVIEW IDPYAK Industrial Pharmacology. (Mount Kisco, NY) V.1-3, 1974-79. Discontinued. Volume(issue)/page/year: 2,209,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5594 No. of Facilities: 69 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 514 (estimated) No. of Female Employees: 266 (estimated)
Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger
Hazard Statements H225-H301 + H311 + H331-H370
Precautionary Statements P210-P260-P280-P301 + P310-P311
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T:Toxic
Risk Phrases R23/24/25;R36/37/38;R42/43;R63
Safety Phrases S22-S26-S36/37/39-S45-S36/37-S16
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS HO9450000
Packaging Group III
Hazard Class 6.1(b)

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title: CAS No. 549-18-8 | Chemsrc address: https://www.chemsrc.com/en/baike/1191391.html

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